Direct Synthesis of N-Protected Serine- and Threonine-Derived Weinreb Amides via Diboronic Acid Anhydride-Catalyzed Dehydrative Amidation: Application to the Concise Synthesis of Garner’s Aldehyde
Naoyuki Shimada, Naoki Ohse, Naoya Takahashi, Sari Urata, Masayoshi Koshizuka, Kazuishi Makino
Abstract
Abstract An efficient method for the direct synthesis of Weinreb amides derived from serine and threonine derivatives via diboronic acid anhydride-catalyzed hydroxy-directed amidation is described. This is the first successful example of the synthesis of serine- or threonine-derived Weinreb amides using catalytic dehydrative amidations. The methodology could be applied to the concise synthesis of Garner’s aldehyde.
Topics & Concepts
ChemistrySerineAldehydeThreonineCatalysisOrganic chemistryCombinatorial chemistryEnzymeChemical Synthesis and AnalysisSynthetic Organic Chemistry MethodsAdvanced Synthetic Organic Chemistry